CH185607A - Process for the preparation of N1N2-di- (2-methyl-4-aminoquinolyl-6) -N3-diethylmelamine. - Google Patents
Process for the preparation of N1N2-di- (2-methyl-4-aminoquinolyl-6) -N3-diethylmelamine.Info
- Publication number
- CH185607A CH185607A CH185607DA CH185607A CH 185607 A CH185607 A CH 185607A CH 185607D A CH185607D A CH 185607DA CH 185607 A CH185607 A CH 185607A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- diethylmelamine
- aminoquinolyl
- preparation
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 150000001875 compounds Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- XKDPIURMGBVXAB-UHFFFAOYSA-N 2-methylquinoline-4,6-diamine Chemical compound C1=C(N)C=CC2=NC(C)=CC(N)=C21 XKDPIURMGBVXAB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 241000287181 Sturnus vulgaris Species 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von NiN2-D1-(2-methyl-4-aminochinolyl-6)-Ns-diäthylmelamin. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung von NiN2-Dl- (2-methyl-4-aminochinolyl- 6)- Ms -diäthylmel- amin, welches dadurch gekennzeichnet ist, dass man etwa 2 Mol 4,
6-Diamino-2-methyl- chinolin mit etwa 1 Mol Cyanurchlorid um setzt und das so erhaltene Dihydrochlorid des NiNs-Di-(2-methyl- 4-aminochinolyl - 6) - chlor- cyanurdiamid mit Diäthylamin behandelt.
Die neue Verbindung bildet ein wasser lösliches Hydrochlorid; sie schmilzt bei 215 bis 220 . Sie soll als Arzneimittel Verwen dung finden.
<I>Beispiel:</I> NiN2-Di-(2-metliyl-4-ami n ochi >j olyl-6)-Ns - diäthylmelamin.
19 g 4.6-Diamino-2-methylchinolin, gelöst in 150 cm' Eisessig, werden unter Rühren bei Wasserbadtemperatur mit 10 g Cyanur- chlorid versetzt. Es bildet sich ein farbloser Brei, der nach etwa zweistündigem Erwärmen abgesaugt und mit heissem Eisessig und Äther gewaschen wird.
Das farblose, feine Pulver stellt das Dihydrochlorid des NiNss-Dl-(2- methyl-4-aminochi nolyl-6)-chlorcyan urdiami d s dar. 6 g dieses Dihydrochlorids werden mit 25 cm' Alkohol und 5 g Diäthylamin 3 Stunden auf 120-125' erhitzt. Dann wird der Rohr inhalt zur Trockne verdampft und der Rück stand in heissem, mit etwas Salzsäure ange säuertem Wasser aufgenommen. Die warme Lösung wird mit Natriumchloridlösung ver setzt und das dadurch abgeschiedene salzsaure Salz der neuen Base abgesaugt und mit ver dünnter Salzsäure und Aceton gewaschen.
Das salzsaure Salz verflüssigt sich beim Trocknen im Wasserbad unter Wasserverlust und er starrt später wieder zu einer grauen, spröden Masse. Ausbeute 5,5 g. Es ist in Wasser gut löslich. Die durch Ammoniak aus der Lösung gefällte farblose Base kann aus Alkohol um kristallisiert werden. Sie schmilzt danach bei 215-2200.
Process for the preparation of NiN2-D1- (2-methyl-4-aminoquinolyl-6) -Ns-diethylmelamine. The subject of the present patent is a process for the preparation of NiN2-Dl- (2-methyl-4-aminochinolyl- 6) - Ms -diethylmelamine, which is characterized in that about 2 moles of 4,
6-diamino-2-methyl-quinoline with about 1 mole of cyanuric chloride and the resulting dihydrochloride of NiNs-di- (2-methyl-4-aminochinolyl-6) - treated with diethylamine.
The new compound forms a water-soluble hydrochloride; it melts at 215 to 220. It should be used as a medicine.
<I> Example: </I> NiN2-Di- (2-methyl-4-ami n ochi> jolyl-6) -Ns - diethylmelamine.
19 g of 4,6-diamino-2-methylquinoline, dissolved in 150 cm of glacial acetic acid, are admixed with 10 g of cyanuric chloride while stirring at the water bath temperature. A colorless paste forms which, after heating for about two hours, is suctioned off and washed with hot glacial acetic acid and ether.
The colorless, fine powder is the dihydrochloride of NiNss-Dl- (2- methyl-4-aminochinolyl-6) -chlorcyan urdiami ds. 6 g of this dihydrochloride are mixed with 25 cm 'of alcohol and 5 g of diethylamine for 3 hours to 120- 125 'heated. The contents of the tube are then evaporated to dryness and the residue is taken up in hot water acidified with a little hydrochloric acid. Sodium chloride solution is added to the warm solution and the resulting hydrochloric acid salt of the new base is filtered off with suction and washed with dilute hydrochloric acid and acetone.
The hydrochloric acid salt liquefies when it is dried in a water bath with loss of water and it later stares back into a gray, brittle mass. Yield 5.5g. It is easily soluble in water. The colorless base precipitated from the solution by ammonia can be recrystallized from alcohol. It then melts at 215-2200.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE185607X | 1932-11-04 | ||
| CH176485T | 1933-10-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH185607A true CH185607A (en) | 1936-07-31 |
Family
ID=25719856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH185607D CH185607A (en) | 1932-11-04 | 1933-10-04 | Process for the preparation of N1N2-di- (2-methyl-4-aminoquinolyl-6) -N3-diethylmelamine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH185607A (en) |
-
1933
- 1933-10-04 CH CH185607D patent/CH185607A/en unknown
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